Mercuri alkyl phenol derivatives



Patented Oct. 8, 1940 i MERCURI ALKYL PHENOL DERIVATIVES Walter G. Christiansen, Glen Ridge, N. J assignor to E. R. Squibb & Sons, New York, N. Y., a corporation of New York No Drawing. Original application September 13,

1934, Serial No. 743,840. Divided and this application August 30, 1938, Serial No. 227,503

Claims. (Cl. 260-433) This invention relates to, and has for its object action mixture is filtered, washed, and dried as in the provision of, certain mercuri alkyl phenol dethe foregoing examples, yielding the desired comrivatives. pound in the form of white crystals.

This case is a division of application Serial No. 5 743,840, filed September 13, 1934, now Patent No. EXAMPLE 2 5 The compounds of this invention are mercuri Hydromymercuri Z-m'tro 4-propyl phenol alkyl phenol derivatives of the group consisting of 0H 10 on 0 N02 HOHg- R R anion-Hg and Hg- 2.3 g. 2-nitro 4-propyl phenol is dissolved in wherein one R represents a member of the group iz ii a gfi iiggfi 53% i 21;3 5: 32 i consisting of halogen and nitro, and the other represents a straight-chain alkyl having at least g Water sthgltly i 0 three carbon atoms. They may be prepared by ace 1 1S M er ours of interacting the corresponding unmercurated z. 3? est 9 dlvalent q f bemg negalkyl phenol derivatives with mercuric acetate 8 Crysta orange prefclpltate the sired compound, is isolated as in the preceding and replaclng the acetoxy with the desired anion exam 1e Purification ma be effect d b di by means of the compound of that anion with 1 p & 1 y 25 an alkali metal (cf. Whitmores Organic Comso 0 an W so {mom m i pounds of Mercury 1921 pp 257 258) These filtering out the slight residue, and preclpltatmg mercuri alkyl phenol derivatives have been found wlth mute acetw to be active germicides. Among the numerous other compounds that The following examples. are illustrative of the m be prepared accordance Wlth the 30 invention: tlon are the following (the chloro, the cyano, the

E LE 1 thlocyano, the nitrato, and the hydroxy com- XMH pounds being formed by treating solutions of the Aceto mercuri l hem acetoxy compound with, respectively, the chloxy 10 (my 10 ride, and cyanide, the thiocyamde, the nitrate,

OH and the hydroxide, of an alkali metal).

1 Anhydromercuri 2-chloro l-normal-butyl phenol. Anhydromercuri 2-ch10ro 4-normal-amy1 phenol.

Chloromercuri 2-chloro 4-propyl phenol. Q Acetoxy mercuri 2-bromo 4-propyl phenol.

- Nitratomercuri 2-nitro 4-norma1-butyl phenol. 4.71 g. 2-chlor0 4-propyl phenol is dissolved in i yanamer -n tm r a1- y1p 0 25 cc. methyl alcohol, and While the solution is Chloromercuri 2-nitr0 p 0py1 ph n l. 45

refluxed on a steam-bath, 8.7 g. mercuri acetate Acetoxymerculi -D py 4-Chl010 p e ol. dissolved in 25 cc. water slightly acidulated with yd y r ur -p 0py1 t 0 p n l. acetic acid is added rapid-dropwise with mechanical stirring. After three hours of refluxing, a The invention may be variously otherwise emtest for divalent mercury being negative, the rebodied within the scope of the appended claims. 50

I claim: 1. Mercuri alkyl phenol derivatives of the group consisting of wherein one B represents a member of the group 15 consisting of halogen and nitro, and the other represents a straight-chain lower alkyl having at least three carbon atoms.

2. Mercuri alkyl phenol derivatives of the group consisting of OH O anion-Hgand g- Gil 

